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Custom Tow Behind Trailer Options?

I'm a full time musician who loves to ride. I'm able to easily transport my acoustic guitar (usually half size) on any of my bikes to my gigs that I don't need amplification.

However when it's time to plug in I want to be able to transport my L1 Bose Sound System, guitar, cords, banner, mic stand and CD's in a trailer towed behind my R1100 GS and/or my K75.

The longest item is 46'' and the widest is 28", I would need a height of about 24" I need consider foam lining the box too.

I've heard of someone using a ski box mounted on a trailer. I would line the box with high density foam or whatever you may think would work best to protect my equipment

That seems that may be the way to go as far as the storage unit is concerned.

Having never towed a trailer on a motorcycle my question is what do I need to be aware of when making choices of trailer length, tongue length, suspension, hitches and anything else I may have missed? I've heard the longer the tongue length the better handling.

Obviously i would need to be aware of my overall length, parking and security.

What do you recommend as the trailer portion? A jet ski trailer seems to make some sense but I haven't looked at an empty one up close, just pictures. Seems I can find used one for around $350-$600. Other suggestions please...

A single jetski trailer might be just about right for your required dimensions. Yes, the longer the tongue length the more stable the tow. You definitely want to have a swivel on the tongue. Rough rule is 1.5 to 2 times the width of the axle. I would upgrade the wheel /tires from 8" to 12".
With the lighter weight of what you are hauling you may want to consider a torsion axle, which can be had with different weight ratings.